Exclusive: Screenwriter William Monahan Talks SIN CITY 2 and THE GAMBLER Remake

One of the most popular Best Picture winners of the past decade was 2006’s The Departed. The film had it all: a legendary director in Martin Scorsese, a star-studded cast that included Leonardo DiCaprio, Matt Damon, Alec Baldwin and Mark Wahlberg, and screenwriter William Monahan. The writer instantly became a household name and he won the Best Adapted Screenplay Oscar. Now, Monahan is hard at work on two highly anticipated projects: a remake of The Gambler and Sin City 2. A remake of the 1974 film starring James Caan, The Gambler reunites Monahan with his Departed director Scorsese and possibly DiCaprio too. The long-awaited Sin City sequel features the return of director Robert Rodriguez, bringing Frank Miller’s graphic novel to life once again.

A few days ago I got to speak with Monahan about his directorial debut London Boulevard (which is currently playing on VOD and opens in theaters November 11th). During the extended interview we talked about a wide variety of subjects and in the coming days you can expect the full interview. However, as a tease, after the jump I’m offering updates on both The Gambler and Sin City 2, including what changes he’s making to The Gambler, how he views remakes, what approach he’s taking to adapting Frank Miller’s material on Sin City and more.

Collider: I read in Variety or the Reporter that The Gambler is something you guys are working on?

Monahan: Yeah, that’s my next job.

So you haven’t started writing it yet?

Monahan: No, I’m finishing up Sin City now and I’ll move directly into The Gambler.

What is it about The Gambler that speaks to you and excites you?

Monahan: Dostoyevsky. I’m going to reset it in a place I’m not going to mention.

It wouldn’t be Boston by any chance?

Monahan: No, no, certainly not Boston. I’m going to reset it in a place that’s very interesting to me at present and dip a little bit back into the Dostoyevsky original.

It’s obviously already been made, The Gambler. Is there anything from the other version that’s going to seep its way in or is this a complete reimagining?

Monahan: It has a good structure. I’ll see how it goes. There are things like the Nazi-hunting angle which are obviously outdated by now. I like the structure. I don’t think the picture is the Passion of St. Theresa, but I think it’s pretty good. If it was unsurpassable I wouldn’t touch it. It’s very 70s. There’s always a great hue and cry when you sign onto a “remake,” and that’s always been sort of annoying me and freaking me out. This profession that we’re in is drama. What drama has been since the beginning is, you restage plays with new casts, or a writer will take a new run at an old story…I don’t have an aversion to quote unquote remakes, because I understand what dramatic writing is, what the dramatic profession has always been about, which is talent, not the pretext for its exhibition. When someone bitches about remakes you know you’re not talking to an English major. There’s a particular mentality, usually male, where men need to insist on the supremacy of one thing, whether it’s a film or a band or a sports team or a motorcycle. It’s like, dude, no one gives a shit, all motorcycles are good, find another way to define yourself.

I’m excited to see your name attached to Sin City 2. To be honest with you, I was very shocked and very happy. How did you first get attached to that?

Monahan: I don’t know, I guess Robert (Rodriguez) went to my agents and asked if I was available. I had a conversation with him and it just went on for two week periods with a reading period in between them. It’s terrific stuff, I love being in that Sin City world and being able to do that hard-boiled kind of thing.

They’ve talked about doing Sin City 2 for years. Is this one of those projects where they’re gunning to get started at a certain point and is there pressure to get the script done?

Monahan: I wouldn’t know anything about that. It’s not the sort of conversation I’d have. I just had a creative conversation.

Sin City is obviously Frank Miller. Are there certain things you’re looking at to bring into your Sin City? How much is it your own imagination?

Monahan: I should qualify my previous response about making things your own when you write them. In this case, my job is essentially to be Frank Miller. I have to, as an improvisational actor, be Frank Miller while simultaneously being Monahan. It’s pretty cool because as a screenwriter, as a dramatist, what you’re doing all the time is inhabiting characters and improvising. In writing drama, there’s a great component of being an improvisational actor and there’s also a component of being an improvisational writer who can inhabit another personality and deliver something in the correct tone. Frank Miller is emphatically Frank Miller. That’s what I wanted to see in Sin City and that’s what I want to see in Sin City 2.

How long have you been actually working on the script?

Monahan: Monday will be the end of my fourth week.

Were you able to create any “Monahan” characters from scratch to add into this script?

Monahan: No, they are the Frank Miller characters.

I’m assuming that you’re writing this knowing that it’s going to be an R-rated picture.

Monahan: Was the first one R-rated? Oh God, it must have been, yeah. I wasn’t even thinking about that. There’s a whole class of shit I never think about. I was just about ready to let my twelve year old watch something the other day and my wife said, “You can’t do that. It’s too bloody.” And I said, “What do you mean ‘it’s bloody?’” Then I watched it and went, “Oh yeah, it is”. But the kids are never frightened by movies because they know especially well that movies are made up. It’s interesting to think that my children know more about the process than many mature critics.

Any teasers for the fans? Something they should be excited about or something that you’re really happy with?

Monahan: I think they should be excited that there’s a second Frank Miller movie coming out with Robert doing it, because Robert’s excited and I’m certainly excited to be able to work on this material. It’s going like a rocket.

Look for the full interview with Monahan in the coming days. However, if you missed my interview with Monahan last year before London Boulevard came out in the UK, click here. It’s an in depth conversation that covers the making of the film and a lot more.